Note: it's the guy who's reluctant in this story, so skip it if that's not what you're looking for!
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In my early 20's, I and a group of friends from school went to Las Vegas for a vacation on a shoestring budget. On the trip was my girlfriend, Jenn, a beautiful girl who was probably a little bit out of my league. She had long dark hair and brown eyes, a caring and sensitive personality, and an easy-going nature that puts you at ease. Plus, I knew that, under the loose-fitting shirts, she hid a spectacular pair of 34D breasts and large wine-colored areolas.
Our relationship was going well, although I admit I was a little underwhelmed by her sex drive. She was much more into massages and long kisses than getting down and dirty. Plus, I'm a night owl and she had a tendency to fall asleep early, so we would sometimes go long stretches without being intimate. All in all, though, I was happy with Jenn and could see us staying together for a long time.
Among the others on the trip was my ex-girlfriend, Emily, as well as her boyfriend, Josh. Emily was very different than Jenn. In some ways, calling her my ex isn't accurate, as she was more of an exclusive fuck-buddy for about a year. I could never get myself to fully commit to her as a girlfriend. Part of the reason was that she was
so
fun and
so
eager to get under the sheets, that I had a hard time seeing her as a serious partner. The other part--and I'll admit I am shallow here--was that I wasn't satisfied with her A-cup tits.
That said, I have to admit that Emily was really hot. Short, slim, and very pale with dark red hair in a bob cut that matched her neatly trimmed red landing strip. Her little breasts were topped with small, hard nipples that were bright pink like chewed bubble gum. What she lacked on top, however, she made up for with gorgeously bulging hips and a soft round ass.
And did I mention the eagerness? Emily is a girl who, with every lingering stare she and posture of her body, seemed to be constantly in heat. She knew how to tease me and make me forget everything else except getting into her pants.
The first time we fucked, she took an inch of me into her tight pussy and a devil's smile appeared on her lips.
"I think you're going to have to stretch me out a little," she told me, "Please don't be shy."
And she wasn't kidding, as I pushed into her, she had the tightest cunt I'd ever felt. Her insides wrapped around me, form-fitting, and massaged every inch of my member. It was like she had been molded specifically to pleasure me.
"I want you to finish first," she would say. "The feeling of hot cum shooting into me gets me off."
I was happy to oblige. It was the longest period of time in my life I went without masturbating because Emily was always there to relieve me, no questions asked. The sex kept me with her for so much longer than we should have been together. In retrospect, I think it was an addiction, because she was so hart to quit. In the end, though, I had to break it off because I hoped to actually settle down some day and Emily wasn't "the one."
Now a year later, I had fully kicked my Emily habit and was happy to be with Jenn. Jenn didn't really know too much about my history with Emily, as they weren't close, and I was happy to keep it that way.
You don't need a ton of money to have fun in Vegas, so the biggest expense we faced was the hotel for the weekend. Rather than tolerating a run-down dump, we stayed on the strip, but decided to save cash by sharing one double queen room. Two beds for eight people meant four to a bed, so Jenn and I ended up cramming into a bed with Emily and Josh.
And that's how I found myself trying to sleep between my girlfriend and my former fuck-buddy late one evening. The room was silent as I laid on my side, turned toward Jenn, with an arm around her. She quickly fell asleep, but I was not feeling particularly tired.
Trying not to make any noise, I started brushing my fingers over one of Jenn's nipples. It became hard and sensitive under my touch. She squirmed a little, indicating with body language that she was not interested. I understood her reluctance, it certainly wasn't the right time with so many people around.
Still, I couldn't help but feel a little aroused from my playing. I continued to lie there awake, wishing that it hadn't been over two weeks since we'd last had sex.
Deep in my lamentations, I hardly noticed that something was brushing up the back of my leg. A knee? No, too small... It's a finger. It traced it way up and over the front of my thigh, right into my boxer shorts, and suddenly a hand was cupping my balls.